CA2419224A1 - Composes heterocycliques se liant avec les recepteurs de chimiokines - Google Patents
Composes heterocycliques se liant avec les recepteurs de chimiokines Download PDFInfo
- Publication number
- CA2419224A1 CA2419224A1 CA002419224A CA2419224A CA2419224A1 CA 2419224 A1 CA2419224 A1 CA 2419224A1 CA 002419224 A CA002419224 A CA 002419224A CA 2419224 A CA2419224 A CA 2419224A CA 2419224 A1 CA2419224 A1 CA 2419224A1
- Authority
- CA
- Canada
- Prior art keywords
- mmol
- tetrahydro
- benzenedimethanamine
- quinolinyl
- nmr
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 102000009410 Chemokine receptor Human genes 0.000 title claims abstract description 33
- 108050000299 Chemokine receptor Proteins 0.000 title claims abstract description 33
- 230000027455 binding Effects 0.000 title description 30
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 188
- -1 hydrobromide salt Chemical class 0.000 claims description 167
- 229920006395 saturated elastomer Polymers 0.000 claims description 40
- 150000003839 salts Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000000651 prodrug Chemical group 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 230000002452 interceptive effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- WEZLIYLAGMXZGO-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound N=1C=CNC=1CNCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 WEZLIYLAGMXZGO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- IIBURQNHZQCMKA-UHFFFAOYSA-N n-(furan-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2OC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 IIBURQNHZQCMKA-UHFFFAOYSA-N 0.000 claims description 2
- NZQJPPFVFICWOR-UHFFFAOYSA-N n-[(1-methylpyrrol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN1C=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 NZQJPPFVFICWOR-UHFFFAOYSA-N 0.000 claims description 2
- RKEIPHNVBYPWQO-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)-1,3-benzoxazol-2-amine Chemical compound C=1C=C(CN(C2C3=NC=CC=C3CCC2)C=2OC3=CC=CC=C3N=2)C=CC=1CNCC1=CC=CC=N1 RKEIPHNVBYPWQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
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- YPTODVXKEJXEET-UHFFFAOYSA-N n-(1h-benzimidazol-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC3=CC=CC=C3N=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 YPTODVXKEJXEET-UHFFFAOYSA-N 0.000 claims 1
- UWDNZPLJAOUFIF-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC=CN=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 UWDNZPLJAOUFIF-UHFFFAOYSA-N 0.000 claims 1
- LHDIGVATAPZAFK-UHFFFAOYSA-N n-(3h-imidazo[4,5-c]pyridin-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC3=CC=NC=C3N=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 LHDIGVATAPZAFK-UHFFFAOYSA-N 0.000 claims 1
- WWCSYVUBGHAPBM-UHFFFAOYSA-N n-[(1-methylbenzimidazol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N=1C2=CC=CC=C2N(C)C=1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 WWCSYVUBGHAPBM-UHFFFAOYSA-N 0.000 claims 1
- CKLHJTZOTREWRN-UHFFFAOYSA-N n-[(5,6-dimethyl-1h-benzimidazol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 CKLHJTZOTREWRN-UHFFFAOYSA-N 0.000 claims 1
- RMCATXSKXPBDNF-UHFFFAOYSA-N n-[(5-ethylthiophen-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound S1C(CC)=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 RMCATXSKXPBDNF-UHFFFAOYSA-N 0.000 claims 1
- VAELNJYCHBNKME-UHFFFAOYSA-N n-[(6-nitro-1h-benzimidazol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N=1C2=CC([N+](=O)[O-])=CC=C2NC=1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 VAELNJYCHBNKME-UHFFFAOYSA-N 0.000 claims 1
- MQVBXWKLLOZAJE-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(1,3-thiazol-2-ylmethyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2SC=CN=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 MQVBXWKLLOZAJE-UHFFFAOYSA-N 0.000 claims 1
- PNDMWKHXWDAICF-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(1h-pyrrol-2-ylmethyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 PNDMWKHXWDAICF-UHFFFAOYSA-N 0.000 claims 1
- WTTKTVHBIVMMDP-UHFFFAOYSA-N n-[[4-[[(5-phenyl-1h-imidazol-2-yl)methyl-(pyridin-2-ylmethyl)amino]methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1NCC(C=C1)=CC=C1CN(CC=1N=CC=CC=1)CC(NC=1)=NC=1C1=CC=CC=C1 WTTKTVHBIVMMDP-UHFFFAOYSA-N 0.000 claims 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 246
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 60
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
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- Pyridine Compounds (AREA)
Abstract
L'invention concerne de nouveaux composés utiles pour le ciblage des récepteurs de chimiokines. Ces composés sont des amines tertiaires complexes.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23289100P | 2000-09-15 | 2000-09-15 | |
| US60/232,891 | 2000-09-15 | ||
| US23451000P | 2000-09-22 | 2000-09-22 | |
| US60/234,510 | 2000-09-22 | ||
| PCT/CA2001/001326 WO2002022600A2 (fr) | 2000-09-15 | 2001-09-17 | Composes heterocycliques se liant avec les recepteurs de chimiokines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2419224A1 true CA2419224A1 (fr) | 2002-03-21 |
Family
ID=26926422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002419224A Abandoned CA2419224A1 (fr) | 2000-09-15 | 2001-09-17 | Composes heterocycliques se liant avec les recepteurs de chimiokines |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US6864265B2 (fr) |
| EP (1) | EP1317445B1 (fr) |
| JP (1) | JP2004508422A (fr) |
| KR (1) | KR20030029998A (fr) |
| CN (1) | CN1457339A (fr) |
| AT (1) | ATE425157T1 (fr) |
| AU (2) | AU2001291569B2 (fr) |
| BR (1) | BR0113930A (fr) |
| CA (1) | CA2419224A1 (fr) |
| DE (1) | DE60137944D1 (fr) |
| ES (1) | ES2325909T3 (fr) |
| HK (1) | HK1052011A1 (fr) |
| HU (1) | HUP0301093A2 (fr) |
| IL (1) | IL154227A0 (fr) |
| MX (1) | MXPA03002326A (fr) |
| NO (1) | NO20031179L (fr) |
| NZ (1) | NZ524420A (fr) |
| PL (1) | PL360932A1 (fr) |
| RU (1) | RU2289581C2 (fr) |
| SG (1) | SG126007A1 (fr) |
| TR (1) | TR200300322T2 (fr) |
| WO (1) | WO2002022600A2 (fr) |
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| US7169750B2 (en) | 2001-07-31 | 2007-01-30 | Anormed, Inc. | Methods to mobilize progenitor/stem cells |
| ES2380009T3 (es) | 2001-07-31 | 2012-05-07 | Genzyme Global S.A.R.L. | Métodos para movilizar las células madre/progenitoras |
| US7354932B2 (en) | 2001-12-21 | 2008-04-08 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds with enhanced efficacy |
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| CN100528846C (zh) * | 2002-09-11 | 2009-08-19 | 株式会社吴羽 | 胺化合物及其用途 |
| EP1608352B1 (fr) | 2003-04-02 | 2009-12-30 | Taigen Biotechnology | Composes polyamine pour le traitement de maladies induites par le recepteur de la chemokine |
| US7504422B2 (en) | 2003-04-02 | 2009-03-17 | Taigen Biotechnology Co. Ltd. | Polyamine compounds |
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| WO2006022454A1 (fr) * | 2004-08-27 | 2006-03-02 | Ono Pharmaceutical Co., Ltd | Composé contenant un groupe basique et utilisation |
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| TW200619206A (en) * | 2004-09-29 | 2006-06-16 | Anormed Inc | Chemokine-binding heterocyclic compound salts, and methods of use thereof |
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| US7538113B2 (en) | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7534796B2 (en) | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7531542B2 (en) | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
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| US20080214562A1 (en) * | 2005-07-11 | 2008-09-04 | Kristjan Gudmundsson | Chemical Compounds |
| CA2619828A1 (fr) | 2005-08-19 | 2007-02-22 | Genzyme Corporation | Methodes permettant d'augmenter l'efficacite d'une chimiotherapie |
| WO2007058322A1 (fr) * | 2005-11-18 | 2007-05-24 | Ono Pharmaceutical Co., Ltd. | Composé contenant un groupe basique et son utilisation |
| US7807704B2 (en) * | 2006-03-30 | 2010-10-05 | Chemocentryx, Inc. | Bicyclic, nitrogen-containing compounds modulating CXCR4 and/or CCXCKR2 |
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| EP2042503B1 (fr) * | 2006-05-16 | 2013-01-30 | Ono Pharmaceutical Co., Ltd. | Composé ayant un groupe acide qui peut être protégé et utilisation dudit composé |
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| JP2010507567A (ja) * | 2006-08-07 | 2010-03-11 | ジェンザイム・コーポレーション | 併用療法 |
| US20110105477A1 (en) * | 2007-09-14 | 2011-05-05 | The Regents Of The University Of Michigan | Compositions and methods relating to hiv protease inhibition |
| BRPI0913879A2 (pt) * | 2008-07-02 | 2019-09-24 | Hoffmann La Roche | fenilpirazinonas como inibidores de quinase |
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| CN104478795A (zh) * | 2014-11-24 | 2015-04-01 | 苏州乔纳森新材料科技有限公司 | 一种2-氯烟醛的制备方法 |
| CA3026154A1 (fr) | 2015-06-03 | 2016-12-08 | The University Of Queensland | Agents mobilisateurs et leurs utilisations |
| CN104945313A (zh) * | 2015-06-19 | 2015-09-30 | 洪帅金 | 一种2-甲基-3-溴吡啶的制备方法 |
| BR112018007021B1 (pt) * | 2015-10-06 | 2024-01-09 | Proteostasis Therapeutics, Inc | Composto, composição compreendendo os ditos compostos e uso dos mesmos para tratar fibrose cística |
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| CN116375650B (zh) * | 2022-12-30 | 2025-08-05 | 浙江美诺华药物化学有限公司 | 一种替戈拉生中间体的制备方法 |
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| RU2024516C1 (ru) * | 1989-02-02 | 1994-12-15 | Яманути Фармасьютикал Ко., Лтд. | Способ получения производного тетрагидробензимидазола или его фармацевтически приемлемой соли |
| US5021409A (en) | 1989-12-21 | 1991-06-04 | Johnson Matthey Plc | Antiviral cyclic polyamines |
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| GB9126677D0 (en) | 1991-12-16 | 1992-02-12 | Johnson Matthey Plc | Improvements in chemical compounds |
| GB9400411D0 (en) | 1994-01-11 | 1994-03-09 | Johnson Matthey Plc | Improvements in chemical compounds |
| GB9511357D0 (en) | 1995-06-06 | 1995-08-02 | Johnson Matthey Plc | Improved antiviral compounds |
| EP1015440A1 (fr) | 1997-07-16 | 2000-07-05 | Ciba SC Holding AG | Spiro composes du type polyglycidyle et leur utilisation dans des resines epoxy |
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| WO2000042852A1 (fr) * | 1999-01-25 | 2000-07-27 | Smithkline Beecham Corporation | Composes et procedes |
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| BR0010655A (pt) * | 1999-03-24 | 2002-02-13 | Anormed Inc | Compostos heterocìclicos para ligação ao receptor de quimiocina |
| US6750348B1 (en) * | 1999-03-24 | 2004-06-15 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds |
| CA2419224A1 (fr) * | 2000-09-15 | 2002-03-21 | Anormed Inc. | Composes heterocycliques se liant avec les recepteurs de chimiokines |
| US6835731B2 (en) * | 2000-09-15 | 2004-12-28 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds |
-
2001
- 2001-09-17 CA CA002419224A patent/CA2419224A1/fr not_active Abandoned
- 2001-09-17 AU AU2001291569A patent/AU2001291569B2/en not_active Ceased
- 2001-09-17 TR TR2003/00322T patent/TR200300322T2/xx unknown
- 2001-09-17 EP EP01971574A patent/EP1317445B1/fr not_active Expired - Lifetime
- 2001-09-17 JP JP2002526853A patent/JP2004508422A/ja active Pending
- 2001-09-17 HK HK03104377.2A patent/HK1052011A1/zh unknown
- 2001-09-17 MX MXPA03002326A patent/MXPA03002326A/es active IP Right Grant
- 2001-09-17 CN CN01815627A patent/CN1457339A/zh active Pending
- 2001-09-17 HU HU0301093A patent/HUP0301093A2/hu unknown
- 2001-09-17 ES ES01971574T patent/ES2325909T3/es not_active Expired - Lifetime
- 2001-09-17 AU AU9156901A patent/AU9156901A/xx active Pending
- 2001-09-17 AT AT01971574T patent/ATE425157T1/de not_active IP Right Cessation
- 2001-09-17 DE DE60137944T patent/DE60137944D1/de not_active Expired - Lifetime
- 2001-09-17 BR BR0113930-4A patent/BR0113930A/pt not_active IP Right Cessation
- 2001-09-17 NZ NZ524420A patent/NZ524420A/en unknown
- 2001-09-17 RU RU2003110577/04A patent/RU2289581C2/ru not_active IP Right Cessation
- 2001-09-17 IL IL15422701A patent/IL154227A0/xx unknown
- 2001-09-17 PL PL36093201A patent/PL360932A1/xx unknown
- 2001-09-17 KR KR10-2003-7003710A patent/KR20030029998A/ko not_active Abandoned
- 2001-09-17 US US09/957,682 patent/US6864265B2/en not_active Expired - Fee Related
- 2001-09-17 SG SG200502184A patent/SG126007A1/en unknown
- 2001-09-17 WO PCT/CA2001/001326 patent/WO2002022600A2/fr not_active Ceased
-
2003
- 2003-03-14 NO NO20031179A patent/NO20031179L/no not_active Application Discontinuation
-
2004
- 2004-06-01 US US10/858,910 patent/US7084155B2/en not_active Expired - Fee Related
-
2006
- 2006-02-02 US US11/345,987 patent/US7396840B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL154227A0 (en) | 2003-07-31 |
| ATE425157T1 (de) | 2009-03-15 |
| BR0113930A (pt) | 2003-06-24 |
| ES2325909T3 (es) | 2009-09-24 |
| EP1317445A2 (fr) | 2003-06-11 |
| US20040220207A1 (en) | 2004-11-04 |
| CN1457339A (zh) | 2003-11-19 |
| AU2001291569B2 (en) | 2007-07-26 |
| US6864265B2 (en) | 2005-03-08 |
| HK1052011A1 (zh) | 2003-08-29 |
| US7084155B2 (en) | 2006-08-01 |
| AU9156901A (en) | 2002-03-26 |
| WO2002022600A2 (fr) | 2002-03-21 |
| NO20031179D0 (no) | 2003-03-14 |
| EP1317445B1 (fr) | 2009-03-11 |
| RU2289581C2 (ru) | 2006-12-20 |
| MXPA03002326A (es) | 2003-06-06 |
| US7396840B2 (en) | 2008-07-08 |
| WO2002022600A3 (fr) | 2002-05-10 |
| KR20030029998A (ko) | 2003-04-16 |
| PL360932A1 (en) | 2004-09-20 |
| JP2004508422A (ja) | 2004-03-18 |
| NO20031179L (no) | 2003-03-14 |
| DE60137944D1 (de) | 2009-04-23 |
| NZ524420A (en) | 2005-04-29 |
| SG126007A1 (en) | 2006-10-30 |
| US20060128750A1 (en) | 2006-06-15 |
| TR200300322T2 (tr) | 2003-09-22 |
| US20030018046A1 (en) | 2003-01-23 |
| HUP0301093A2 (hu) | 2003-09-29 |
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